We Lost Ourselves on the Way to Paradise
by deafwinchester
Summary: Dean is rough-and-tumble, content with his hair cropped close to his head, and more than willing to imitate his daddy's mannerisms and dress. He likes cars and fighting and all things physical, he likes his burgers with a side of grease, and he's all things butch that make his younger brother Sammy look girlish in comparison. But it's never really been that simple. (MTF!Dean)


**Warnings:** Gender dysphoria, canonical alcoholism and torture.

 **Author's Note:** Please note that pronouns are used intentionally and based on how Deanna conceived of herself at the time. Additionally, there is no "typical" transgender story of self-realization and everything is very individual. Deanna's experiences are her own and are not meant to represent those of trans people as a whole.

This fic is crossposted on ArchiveOfOurOwn, LiveJournal, and Tumblr

 **We Lost Ourselves on the Way to Paradise**

by deafwinchester

The narrative that gets repeated in the media again and again is a simple one. Known since you were the age of four, tried to cut your penis off with your mother's nail clippers, never a moment's doubt, blah, blah, _blah_ , wore your mother's makeup and cried when she tried to cut your hair, played with Barbies, and never played with boys, blah, blah, _blah_. It's the most often repeated narrative because it's the narrative that's most palatable to an ignorant audience, one that makes it seem like a "must be true" rather than "as if!" because four year olds are innocents, not perverts or inverts or sexual deviants, because continuity implies credibility and people are desperate for an answer. And for some, it's even the truth.

But this is not Dean's narrative, and the differences between his reality and the reality portrayed by the media and propagated by the pulpit and the classroom collude any understanding of his situation that he might have been able to glean otherwise. There are never any blatant signs, not really, when he's a young child, and so, when he finally figures it out, it's that much harder to accept and fully understand.

To the average observer, young Dean is very much the boy he appears to be and his birth certificate attests to. He's rough-and-tumble, content with his hair cropped close to his head, and more than willing to imitate his daddy's mannerisms and dress. He likes cars and fighting and all things physical, he likes his burgers with a side of grease, and he's all things butch that make his younger brother Sammy look girlish in comparison.

Yet when people call Dean "boy" or "son" or "young man," a frission of negative energy washes over him, snakes down his spine. It doesn't matter the context, whether "boy" is meant as a compliment or pejorative, used kindly or in a harsh tone. All Dean knows is that regardless of whether these words are intended as praise or criticism, he just wants the person uttering the words to _shut up already_. He knows he doesn't like to use these words in reference to himself or hear them used in reference to himself, but he just can't escape their venomous touch either.

The Winchester family moves around frequently throughout Dean's childhood, but sometimes, they stick around long enough for Dean to get a taste of what being an ordinary child is like. When he's not doing his classwork (which is just about always), he has time to observe his classmates. And so early on in middle school when he sees the changes his female classmates are undergoing, what with all their budding breasts and talk of periods, all he feels is hot, prickling jealousy underneath his skin, and he doesn't know why.

He turns out to be a bit of a late bloomer, reaching puberty just a bit later than most of his other classmates, but when it finally reaches him, the changes to his body that he had before only thought of in a theoretical, dispassionate light unnerve him deeply. More and more, when he looks into the mirror, he feels as if a different person entirely is looking at him. He's not crazy; he knows, intellectually, that his reflection is correct, that he is the person represented in the mirror, but each time he checks his appearance, there's a moment when he thinks his reflection is a stranger.

Erections are a completely mortifying experience for Dean. It doesn't matter if no one else sees it because _Dean_ knows it's there and for some reason unknowable to Dean, it feels wrong. Not wrong as in evil like the creatures his family fights, but wrong as in it shouldn't occur at all. One day, he sees a roll of duct tape in the trunk of his father's car and get the idea of taping his genitals down so that he doesn't have to put up with the problem anymore. But the duct tape quickly becomes a problem in and of itself—when Dean tries to remove it, it hurts like a sonofabitch and the skin even tears in a few places and becomes inflamed in the form of a bumpy red rash in others. The pain doesn't dissuade him and he tries a few more times before he finds out the duct tape impedes his movement on hunts. Getting erections might be mortifying and _bad wrong no_ but it's not worth getting Sammy killed over. He deals.

When Dean is nineteen, he has a short-lived fling with a girl named Rhonda Hurley. She's kinky in a way that isn't alarming and introduces him to a kind of sex he had barely even imagined before. One of the many things she has him do in bed is to try on her pretty pink satin panties. And he _likes_ it and it _should_ be embarrassing, but it isn't. Somehow it feels right, and the feelings have nothing to do with sex even in such a sexually charged situation. Dean feels pretty, which is something he's never felt like in his entire life, and he likes it. Rhonda strokes his cock through the panties, calls it his _pussy_ , and lets him rut into her hand. It's all a bit overwhelming and he ends up burying his face in Rhonda's shoulder, whining, and when he comes, she strokes his back through the aftershocks. She seems amused, with a knowing twinkle in her eye, at his strong reaction to the whole experience. Once he's had time to regroup, she has him eat her out and praises him, calling him her "good girl" when he does something that's particularly to her liking. The phrasing makes him feel warm all over and if he weren't so occupied with making Rhonda feel good, he might have cried. (He did cry, later, after she was gone. He didn't know why it all hurt so damn bad.)

He tries to forget. It's impossible and yet he almost manages. Between hunts and a constant flow of women and whiskey, it's easy to ignore the way he feels most of the time. But most of the time is certainly not always, and there are times where no amount of sex or booze can soothe the ache he feels. Between a lifetime of hunting and forever being unsettled and whatever the hell _this_ is that he doesn't have a name for, it's no wonder that Dean's a little bit broken.

He pockets a 99-cent bottle of cheap glittery nail polish at a Gas-N-Sip one day when he's on a food run. He doesn't have the guts to pay for it and figures it won't be missed. It isn't until two weeks later that he gets enough time alone and enough courage to use it, and he clumsily paints a heavily-streaked coat over his toenails. He can't bear to have anyone see the evidence and so he doesn't risk painting his fingernails as well, and just thirty minutes after putting it on, he chips it all off, cursing his foolishness and telling himself that with how often he and Sam seem to wake up in hospitals or lose their clothes during hunts, it's too much of a risk. It's not really his taste anyway, but he . . . he just wanted to know what it was like, just for a little while.

Dean knows that people think he's overcompensating, and maybe they're right (they almost certainly are), but it's not in the way that they think. He likes women, likes their curves and their smiles and the taste of their skin, likes to make them shiver with anticipation and quiver with pleasure. And he honestly can't say that men hold much of an appeal for him in that way. He's not faking that, not ever. But more than that, Dean _is_ masculine, _is_ whiskey and gun powder and fist fights and grease and the polished metal of the Impala. And yet, he still feels wrong, still feels like his skin itches and doesn't fit right across the set of his bones, still knows that certain things are off-limits to him and always have been and he is too damn scared to cross that line and see if doing so would soothe this lifelong itch.

Demons don't play nice and they make proficient use of any and all suitable ammunition they have against him in Hell. They are determined to break him, to make him snap, to turn him into the same twisted, no-longer-human scum that they are made of. And the worst part is that they know practically every detail of his life and so they are efficient at getting in his head. His childhood, his mother, his brother, his father, Bobby, every girl he's ever gotten close to, every person he's ever cared about . . . none of it is off-limits. They know his fears and his insecurities, they know about his perverted sense of family loyalty, they know about Rhonda Hurley and the duct tape and Lisa and the way he grew up hoping he'd one day be as beautiful as his mom and how jealous he feels of women and they use it all against him, not because they even remotely care but because they know where to drive the knives and when to twist them and tear at his flesh and when to torment.

Leaving Hell is a blessing, a breath of fresh air, but it's also hard in a way almost nothing really ever has been, in a way that nothing ever really can be, because he is _broken_ and he can never be fixed. He hardly sleeps and he self-medicates with a bottle of jack and an endless line of hot women, but it's not enough. It can never be enough, but between the Apocalypse and the constant threat of worldwide destruction and the death of the people he loves, it has to be. He squashes down all the tormented emotions and memories of demonic taunts and his own agonized screaming, grinds them into the dirt with the heel of his steel-toed boots and tries to pretend they don't exist. And if he wakes gasping and choking on a nightmare, if he can't quite shake the feeling of wrongness (wrong that he's not dead, wrong that he's broken, wrong that his skin doesn't fit), he knows he earned it when he first drew blood in Hell. He . . . _endures_.

It's not Hell or the angels or any of the pagan gods or anything supernatural that almost undoes him; it's Lisa. She is gentle and kind but she takes none of his nonsense, instead taking him apart bit by bit and removing layers that only serve to hurt him. Her love aches in the best way possible and he finds himself opening up to her in a way he hasn't really had the chance to do with anyone before. And in the quiet after the abridged Apocalypse, he has a chance to settle. His _sense of self_ starts to settle, but as most things in his life, it's brought to an end all too soon and he finds himself feeling even more broken than before. He can't have Lisa, he can't have Ben, and he can't have whatever idyllic life he was starting to hope he could secure for himself. He has to be Dean, Dean the Hunter, Dean the eternal fuckup.

It's not until years later, sitting in a dingy bar with a tipsy, giggly Charlie Bradbury at his side and an appletini in his hand that he actually fesses up, dares to say aloud what he'd so long refused to put a name to. The girlie drinks she's plied him with aren't exactly straight whiskey, but they pack a serious punch, and in the company of someone as warm as Charlie Bradbury, he finds himself warm and loose and _comfortable_ in a way he hasn't been in a long time. He tells her just how wrong he's felt practically all his life, tells her _how_ he's felt wrong, and she is the one who cautiously suggests a word for his unease and pain that just might fit. The word is eleven letters long, just three syllables, and it does no justice to the deep-seated, terrible wrongness he's endured in its brevity and simplicity, but it fits _. Transgender_. It's a word that he's heard before and even knew the meaning of and he's even met people fitting its definition before but never dared consider it in reference to himself. But it fits, it fits, it fits, and it eases some measure of the ache knotted deep in his chest. Or would it be—? _Right_. Her chest.

The morning after her ill-advised drinking session with Charlie, she almost considers taking it all back and trying to pretend that the whole ordeal never happened. But Charlie doesn't throw any of it in her face, doesn't make her feel the least bit bad for having said what she did or being who she is. And so she doesn't take it back and Charlie becomes her advocate in so many ways. She's there when she tells Sam and can barely get the words out, almost choking on the air it takes to complete them. She's there when Sam snorts his disbelief and brings up her womanizing ways and butch behavior and makes her feel like a fraud. She keeps an eye on her when she drowns her pain in whiskey and runs interference while Sam comes around. She helps her procure hormones illegally, but she never pushes her in that direction. Mostly, she just keeps her feeling human.

And Sam _does_ come around, feels like an ass when he realizes that she is completely serious. And when he looks back on their shared childhood and lifetime together, he can see just how much his bro—no _, sister_ had been hurting and even see signs that he had never noticed. When he comes to that realization, he does his damnedest to be supportive of his big sister in the best ways he knows how.

At first, Deanna is somewhat resistant to the idea of transition. After all, she has been in this body for three and a half decades and it has served her well. But once she has accepted who she is and let herself acknowledge her gender, she can't shake the appeal of soothing the discord she feels in her own body, of being perceived as the woman she knows she is, and she makes that leap. It's Charlie who procures the hormones and testosterone blockers for her and ensures that it's as safe as it can be. With their lives as hectic as they are and so threatened by supernatural creatures and law enforcement alike, it's difficult for Deanna to keep up with an ethical doctor, and so they prepare blood samples at the bunker and send them off to a contact of Charlie's for testing. It's the best they can do to make sure that nothing goes wrong.

It helps that despite her tall frame, she has some feminine features. Delicate facial structure, wide eyes and plush lips, the sweet dusting of freckles across her nose and cheeks . . . they all make it a bit easier for her when she does start trying to pass. Other girls in the same position might not be so lucky, and she's grateful for it. But she still has the wide shoulders and narrow hips to make up for, and lifetimes' worth of hunting and harsh physical labor and fighting have left her with muscular definition that she finds it hard to hide. The estrogen helps, but it takes time for her body's muscles and fat to redistribute into a more feminine form. She resents that it's hard for her to look as she does and dress as she wishes and still be perceived as a woman. She toys with the idea of growing out her hair and wearing traditionally feminine clothes to help, but it's not her and the idea is grating. But slowly she does switch to a more feminized version of her close-cropped hair, starts wearing clothes with a more feminine cut and fit that still suits her tastes, and sometimes puts on light makeup like lipstick and mascara. Slowly, she becomes more at home in her own body and so much gets easier after that.

She is a hunter. She was born in Lawrence, Kansas in the winter of 1979. She enjoys sunsets, long walks on the beach, and frisky women. She likes double bacon cheeseburgers and whiskey and she keeps a knife under her pillow and a gun in close reach and she keeps her hair cropped short and, on occasion, she wears lipstick.

She _is_ Deanna Winchester and it doesn't matter what anyone else thinks.


End file.
